Triethylborane (TEB) was found to be a mild, efficient, and acid catalyst in electrophilic
substitution reaction of indoles with aldehydes compounds to afford the corresponding
bis(indolyl)methanes. Vibrindole A (5) and bis(indolyl)methanes derivatives 16 and 18 were
synthesized using this methodology. Compound 16 is an intermediary in the synthesis of the natural
bisindoles arsindoline B (2) and streptindole (6). The structure of vibrindole A (5) was unequivocally confirmed by a single
crystal X-ray diffraction analysis.
Keywords: Arsindoline B, bis(indolyl)methanes, indole, streptindole, triethylborane.
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